


Righteous Side of Hell

by 015wayward_winchester



Series: Balance [2]
Category: Supernatural
Genre: Castiel and Dean Winchester Need to Use Their Words, Castiel is Claire Novak's Parent, Castiel is Jack Kline's Parent, Castiel is Loved (Supernatural), Castiel is Protective of Dean Winchester, Castiel is a Winchester (Supernatural), Castiel/Dean Winchester First Kiss, Character Death, Chuck is a dick, Dad Castiel, Dean Winchester is Jack Kline's Parent, Dean Winchester is Loved, Dean Winchester is Protective of Sam Winchester, Death, Heaven, Hell, Idiots in Love, M/M, Perdition, Protective Sam Winchester, Sam Winchester is Jack Kline's Parent, Torture, Tortured Castiel (Supernatural), Tortured Winchesters, sabriel if you squint
Language: English
Status: Completed
Published: 2020-12-16
Updated: 2020-12-16
Packaged: 2021-03-09 19:46:57
Rating: Not Rated
Warnings: Major Character Death
Chapters: 11
Words: 4,453
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27951785
Author URL: https://archiveofourown.org/users/015wayward_winchester/pseuds/015wayward_winchester
Summary: Part two of “Wrong Side of Heaven”Sam, Cas, Jack, Rowena, and Gabriel will stop at nothing to Pull Dean out of Hell. Taking Chuck down is a bonus.
Relationships: Castiel/Dean Winchester, Dean Winchester & Sam Winchester, Gabriel/Sam Winchester
Series: Balance [2]
Series URL: https://archiveofourown.org/series/2045705
Comments: 2
Kudos: 17





	1. Chapter 1

Castiel’s POV

No. Dean was in Hell. His head was spinning. He had to raise him from perdition. He had to. 

Chuck hadn’t noticed Cas had stopped moving, or more likely he just didn’t care.

He couldn’t just barge into Hell with a half cocked plan. That would send him to the empty and who knows what Chuck would do to the brothers? No he had to find Sam. Sam always had a plan especially where saving his brother was involved. 

He made his way through the bright hallways until he saw a nameplate ‘Sam Winchester’. He couldn’t help but chuckle at all the listed death years. He opened the door. 

“Sam! Sam!”

“Cas?” Sam questioned “what damn memory is this?” 

“I’m not a memory. It’s me.”

Sam ran over to hug him.

“It’s good to see you Cas” they broke away “wait you were dead. In the empty. How’d you get out?”

“I was brought up by Chuck” Before Sam could ask why Cas grabbed a piece of paper and wrote ‘I want to help. We have to save Dean’ 

Sam nodded 

Cas continued writing ‘Gabriel is helping me. He’ll set up some sort of sigil so we can talk. Do you have any sort of plan?’

Sam shock his head sorrowfully

“Have you seen Jack?” He asked worriedly 

Not the safest conversation but he couldn’t lie to Sam. He’d been through enough.

“Yes I have. He’s about as well as can be expected. I sent Claire over so he wouldn’t be alone.” Cas needed to find Gabriel “I have a few things to take care of. I’ll be back when I can” 

“Be safe Cas. Don’t do anything Dean and me wouldn’t do.”

Cas had to laugh “there’s nothing you boys wouldn’t do for family”

“Damn straight”


	2. Chapter 2

Gabriel’s POV

He saw Cas coming down a hallway. Gabriel quickly rushed over and whispered.

“I got it. I just need to find Sam’s Heaven.”

Cas whispered back “down this hallway on the right”

“Cas I know that look. What are you doing?” 

“I need to speak with Rowena.”

“How the fuck are you going to manage that? Dad is watching every move you make. You can’t just barge into Hell.”

“I’ll figure something out”

With that Cas walked away.

“Shit” Gabriel whispered under his breath

Cas had never been impulsive or desperate before. Spending so many years on Earth, especially with the Winchesters he must’ve learned a thing or two. 

Hopefully Cas could handle himself. He had a sigil to draw.

Gabriel entered Sam’s Heaven and reached behind the scenery to draw the symbol. It was similar to a banishment sigil, but with a few extra lines.

“Gabriel? Is this a memory”

“Nope.” He put a drop of his blood into the sigil and it glowed blue. “This will keep us from being overheard in here. All Chuck will hear is the memory we’re in.”

Sam walked over slowly. 

“It’s really you?”

“Yeah Sam I’m here”

Sam put his arms around the angel. After pulling away Sam asked

“So same story as Cas? Chuck pulled you out?”

“Yeah that seems to be the case.”

“Why would he do that? No offense but you are two of the most rebellious angels.”

Gabriel shrugged in acknowledgment “I had no idea why he pulled us out at first, but now I have an idea. We’re the two angels that whenever we took a stand, we stood with you. So I think Chuck wants us to see where that led. He wants us to think we failed and regret our choices”

“Do you?” 

“I will never regret standing alongside you and your brother.” He took a pause before continuing “any leads on how to save him?”

“Yes. I have something, but there has to be something else.” Sam pulled out a Bible page “I didn’t want to show it to Cas just yet” he admitted

Gabriel read the page “end of time no. Who knows if time can even end? We’ll find something else.”


	3. Chapter 3

Rowena’s POV

Rowena enjoyed running Hell. Not because she had the power to inflict torture, but because she had the power to limit it. She shut down all crossroads deals because Fergus could’ve spent eternity at peace in Heaven, but instead lived an afterlife of torment. If she could save anyone from his fate she was doing good. She limited the racks to those who truly deserved to be there except for Dean. Oh that poor boy. He deserved so much better. After a lifetime of saving people and destroying his life to save the world he belonged in Heaven, and Rowena spent every free moment searching for something to help him. She felt a soft breeze behind her. That was very strange. She turned around.

“Castiel?” She questioned “what in the Heaven are you doing down here?”

“My father had some messages for you. I’m sure he suspects I have ulterior motives for wanting to be the messenger, but he thinks he’s won. He has no need to worry. I think part of him wants me down here. To see the broken man I stood beside” 

“Cas Dean is not broken. He’s staying strong determined not to break. When he needs strength he thinks of you and Sam. I know this isn’t much but your father and I have a deal. Every 1,200 Hell years he gets one year break from the rack. Come and see him.”

“Thank you. You’re right it’s not much, but it’s better than never getting to step off and it wouldn’t have happened without you.”

Rowena was surprised. How did he know she had done anything? He had a low opinion of her especially in the first few years.

Cas continued as if he could read her mind “I know Dean. He’d instantly accept torture believing he deserved it. There’s no way he struck that bargin”

There really was something between these two. How had they not noticed through the years. 

“I need to return to Heaven. I’ll be back with any messages, plans, and I’ll definitely be back when he’s off the rack.” 

“Of course. Good luck Castiel. Tell Samuel I said hello”

Cas nodded and disappeared. Rowena made her way over to Dean’s rack and demanded the demons left them for a minute.

“Rowena? What’s going on?” Dean asked in a quiet voice

“I haven’t found anything to save you yet, but I just had a visitor. Castiel is alive-“

Dean interrupted “Cas? Is he ok? Where is he?”

“Castiel is alright he’s been pulled from the empty and he’s working with Sam to save you. You’ll be up there in no time”

The demons started coming back

“Thank you” Dean said sincerely

She nodded “Of course. With everything you’ve gone through you deserved a spot of good news” she said with a hint of guilt in her voice

“Listen to me. This isn’t you fault. This is all on Chuck. You did everything you could and you’re still trying to help. Thank you”

“You’re very welcome Dean Winchester.” With that she turned away before the tears could fall. The boy deserved so much better.


	4. Chapter 4

Cas’s POV

Cas, Bobby, Gabriel, and Sam spent many hours a day for what felt like years, damn time was strange here, inside the safety of Sam’s Heaven trying to find anything to save Dean. So far nothing. Occasionally he would pop down to Earth to visit Jack both to make sure his son was ok and keep him in the loop. Jack had been conducting his own research alongside Claire, but they hadn’t found anything yet. On occasion he’d deliver messages for Hell and talk to Rowena about her discoveries. Frustratingly she was also empty handed.

Eventually 1,200 Hell years were up. This was a visit Chuck could not know about so he enlisted the help of Balthazar and Gabriel to distract Chuck for the day. He brought an envelope of some letters Sam and Bobby had written and the Bible page and translation for what was unfortunately their only current plan. 

Cas was nervous. He hadn’t seen Dean since his confession. He had to keep it short and business like in case Dean didn’t feel the same.

He flew into Hell easily. The demons knew they’d face Rowena’s wrath if they documented his arrival or gave him a hard time. He flew to the library where Dean was most likely to be. 

“Hello Dean” he said quietly

“Cas?” Dean asked before embracing him in a tight hug.

“Dean I don’t have much time. If Chuck finds out I came to see you I die, and you and Sam go to the empty. Where you’re not a threat to his ending”

Cas had suspected something along those lines, but Gabriel had confirmed it.

He held out the envelope.

“Sam and Bobby sent this for you. If you have anything for them give it to Rowena. I’ll pop in from time to time but for all our sakes contact between us has to be limited”

“Cas wait.” Dean paused “there’s something I need to say. Ever since you pulled me out of Hell all those years ago I had a feeling. I pushed it down because I didn’t want to complicate or ruin anything, but when you told me you you felt I was shell shocked. I couldn’t respond, and I’m sorry for that. What I have to say can only be said in Spanish”

Cas didn’t know what to think. Was it possible he was truly loved?

“Dean-“ he started before being interrupted

“Yo a tí Cas”

Why did everything sound so much sexier in Spanish?

Dean kissed him. The heat of Hell melted away and it was just the two of them in the middle of the universe.

“Oh hello boys” Rowena had walked in. She was completely unfazed at the sight in front of her. “Oh don’t give me that look Dean. Even a blind man could see the sexual tension between you two.”

Had he really been that obvious? 

Cas coughed “I should be going now.” He didn’t want to leave, but his brothers could only hide his absence for so long. He looked at Dean “I will be back to save you”

“I know you will” Dean replied with such faith

With that Cas flew back to Heaven, but it felt more like he Heaven was behind him, and Hell ahead.


	5. Chapter 5

Claire’s POV

It had been 10 years since Sam and Dean had died and they were still no closer to getting Dean out of Hell. She and Jack had spent their months tearing through the library. On occasion Cas would show up to update them on nonexistent findings, but she knew the real reason he visited was because he wanted to make sure that they were taking care of themselves. 

“Jack why don’t you get some sleep?” She asked “I’ll keep looking” she knew he didn’t need a lot of sleep, but he was drained. 

She made her way to the back corner of the library. She noticed a hinge on the bookshelf. 

“That’s normal” she muttered and started feeling around the books. Maybe one opened the door. Eventually she reached what appeared to be a think leather bound text, but it was stone cold. She pulled on it and that section of the shelf opened revealing texts that looked as old as Castiel, well maybe not that old. She grabbed one and started reading.

After a few hours she’d gone through 3 and was in the middle of a 4th. She found a ritual. One that would resurrect Death. Not Billie, but Death. She remembered hearing about him from Dean. She smiled at the memory. 

“Can you believe it? He thinks he’ll reap god” 

The memory faded leaving her with an idea. What if they were going about this all wrong? They couldn’t save Dean. Not while Chuck was alive, but if Death could reap him they might stand a chance. A snowball’s chance, but still a chance. 

“Jack!” She ran to his room. She felt bad for waking him up, but he’d want to know and it was important they implement any plan as soon as possible. 

“Huh?” He asked sleepily

“I found something” she quickly brought him up to speed

“We need to call Cas” he responded


	6. Chapter 6

Castiel’s POV

He had just gotten back to Heaven. His brothers had done perfectly distracting Chuck for the day. He wandered Heaven aimlessly in the bliss of being loved back, and remembering the kiss they’d shared. Suddenly he started receiving prayers. It was Claire and Jack.

“Cas please come as soon as you can. We found something. It’s a small chance, but still it’s a chance.”

Cas instantly started flying to the bunker. His only thought was saving Dean. He was even more desperate than anything to get him out.

He reached the bunker.

“What have you found” he asked instantly 

“It’s not much” Claire began nervously

“I’ll take anything” Cas responded desperately 

Claire pulled out a book. “We can resurrect Death”

“Billie?! No. She stays in the empty”

Jack put a hand on Cas’s shoulder. “No not Billie. Death. As in the original Death” he explained the plan.

“No.”

“What do you mean no?” Jack asked frustrated “this is the only thing that gives us a chance. The only thing that gives Dean a chance. How can you just say no?”

“Because with Sam and Dean gone the only ones who can summon the horseman are the two of you, and I’m not letting either of you summon Death. You’re kids”

Claire sighed “I’m not a kid anymore Cas. I’m 29 years old. After everything Dean did for me I owe it to him to try” 

Cas nodded. He didn’t like it but he nodded.

“and I-“ Jack started

“No” Cas instantly shut him down. “Jack you’re only 12. You’re still a kid. You’re my son-“

“Dad” Jack interrupted “I’m not a kid. I grew up fast.”

“Too fast” Cas muttered. He still remembered the nursery he had set up with Kelly, all the diapers he bought, and the wide eyed innocence in the boy.

Jack continued “I was raised by Winchesters. While it wasn’t easy I learned. I learned to stand with family. You, Sam, and Dean are my family. Let me do this” 

Cas broke down and hugged his son, and looked to the girl who was just like a daughter to him. Claire joined in on the hug. “I don’t like this, but I have to allow it. I’d make the same choice in your position. I’m so proud to call you my kids”

“Let’s do this” Claire said

The three of them set up the ritual. Jack read the incantation and Claire set up the ingredients. Suddenly there was a flash of light and Death stood before them.

“You rang?” He asked in a low voice

Cas explained the situation, Death was completely unfazed. 

Jack spoke up. “You’re not surprised. You knew this was going to happen” 

“Well of course I knew. I read my own death book. I never had one until Dean Winchester made a deal at a crossroads. He tipped a domino. But that’s the Winchesters for you”

Cas, Jack, and Claire let out a chuckle. 

“So can you do it?” Cas questioned

“Oh yes, but more dominoes have to fall into place”


	7. Chapter 7

Sam’s POV

Cas had called the team, including Balthazar, to his Heaven. Something was definitely up. Everyone was settled around the table. At the moment it was the long table in the map room in the bunker. Finally Cas started speaking.

“Guys we’ve been going about this the wrong way. Everything we do find is useless as long as Chuck is calling the shots, and with him in charge we’ll never save Dean”

Sam completed the thought “so in order to save Dean we need to take down Chuck, and only then do we stand a chance at saving my brother” 

“Yes”

Gabriel stepped in “So his exactly are we going to just end Chuck?”

“We dig” Bobby answered 

“Yeah sure let’s say you find something.” Gabriel began

Cas stepped in “We already have” 

Sam looked up curiously. This morning they had nothing. Now all of a sudden there was a plan?

Cas continued “Jack, Claire, and I have resurrected Death”

“Billie?” Sam interrupted. Cas seriously was not stupid enough to bring her back. 

“No not Billie. Death. The original Death. He has the power to reap god”

“Then what?” Balthazar cut in “The world can’t exactly carry on without a god”

“Unfortunately he’s correct” Gabriel stated

“Jack could take over” Cas said slowly. How was this just coming to him? “Before Jack was born I glimpsed into his mind and saw paradise. A world with no hunger, plague, or crime. This is his destiny”

“No” Sam stepped in “Jack is a kid Cas. Our kid. We can’t ask him to do that.”

“No he was a kid. Then Kelly died, then I died, then I came back and he died, and on and on until we all died. He’s not a kid, and he wants to save the world.”

“It’s too much for him to shoulder alone.” Sam argued 

“Who says he’ll be alone? We’ll be up here to help him, guide him. He can do it.”

“I hardly know the kid, but if you think this is the right move I’ll back your play” Gabriel said

“Castiel we fought together for years. If you trust this Jack I’ll stand with you.” Balthazar agreed 

Cas and Bobby looked at Sam.

“Sam I’m not going to do anything without your support” Cas assured him “But think of your brother. If there’s even a snowball’s chance we can save him shouldn’t we try?”

Bobby who had been silent the whole time finally spoke “I agree with Cas. We need to save Dean, but I don’t know this kid, and I only trust one of these angels. Sam I’ve known you since you were a boy. If you have faith in this kid I say let’s do it, but I’ll follow your lead”

He thought for a moment, but what was there to think about? This was Dean rotting in Hell for him. Again. Cas was absolutely right if there was the slightest chance he had to take it.

“I’m in. Let’s take this son of a bitch down”


	8. Chapter 8

Castiel’s POV

After receiving permission from Sam Cas flew back to the bunker.

“They’re in” he told Death, Jack, and Claire. “We can take down Chuck, but” He looked at Jack “the next part is up to you. You tell me no and we’ll drop it and find something else ok.”

“Cas you’re scaring me. What’s going on?” Jack asked worriedly. 

It didn’t occur to him at the time, but Cas would later realize Jack was worried there was a sacrifice or something of that nature involved.

“After Chuck is gone someone needs to take over, and there’s only one candidate”

“Me” Jack realized

“Yes. I know it’s a lot to ask.”

“No I don’t want that much power.” Jack started

Claire jumped in “that’s exactly why you should do it. Those who don’t want power are often the least likely to abuse it. Jack I’d be more worried if you wanted it”

“The girl is right Jack.” Death stated “this is your destiny. You can save everyone”

Jack looked from Death, to Claire, and finally to Cas. “I’ll do it, but I can’t do it alone. I won’t be the only one in power. I want you and the other angels to help me to keep me from becoming Chuck”

He’d never been so proud of his son. He was in position to become the ultimate power in the entire cosmos, and he found a way to share the power and keep himself in check.

“Of course”

Jack looked at Death “what do I have to do”

“Oh it’s fairly simple, you and I sneak up to Heaven separate Amara and her brother, reap Chuck and transfer his power to you”

“You call that simple?” Cas said at the same time as Claire

“Yes as a matter I do. I can hide us so Chuck doesn’t see anything coming.”

“I-“ Cas began

“Oh Castiel if it makes you feel more comfortable you are more than welcome to accompany us. Chuck won’t suspect anything from you so maybe you and your loyal brothers can get Chuck into position” 

“I think we can manage that”

Cas flew back to Heaven to find his brothers. Oh Chuck was going down.


	9. Chapter 9

Castiel’s POV

He had found Balthazar and Gabriel and they formed a plan. They agreed it would be easiest to trap Chuck in the throne room partly because the son of a bitch spent a large percentage of his time there. 

Gabriel had snuck Sam out of his Heaven.

“You can’t be here. It’s a tight and risky plan as it is.” Cas tried to protest.

Gabriel responded before Sam could “Dad took everything from him: his life, his parents, a lot of girlfriends, and lastly his brother. I think he deserves to watch him go down”

“Cas please” Sam was almost begging and giving him the puppy eyes that no one could deny

“Alright, but stay behind us. If you get hurt on our watch Dean will kill us.”

Cas didn’t like it, but Gabriel was right. After everything Chuck had done Sam deserved to at the very least witness a little payback.

An half an hour later the three angels got into position. They knew Death and Jack were in Heaven due to the timetable they had agreed upon for the plan. Jack sent quick prayers to the three angels as a signal to enter the throne room.

The angels surrounded their father.

“What is the meaning of this?” Chuck demanded “I saved you. I raised you all from the empty and this is what I get? Your little coup. Too bad it won’t be a long little rebellion. I raised you from the empty and I can throw you right back in”

“Dad why are you surprised at this point?” Gabriel responded “we didn’t ask to be brought back you just did it, and might I add you saved the three most rebellious angels who are know to stand beside the flannel wearing hunters. Balthazar the angel who faked his own death and stole Heaven’s weapons to sell in Earth.”

“Guilty. No regrets”

Gabriel continued “Castiel the angel who fell in love with humanity, also known as Dean Winchester, fought alongside them for years to come. Even fighting against you”

Cas just shrugged. Gabriel spoke the truth.

“And me. I ran from Heaven millennia ago. Learned the ways of the tricksters, fought against your apocalypse, and died for the Winchesters. So who’s really to blame for our betrayal? You who brought back the angels with the biggest problems with authority? Or ours for being who we always were”

“I’d say it’s your fault Chuck” Sam stepped out from behind Cas and Gabriel 

“Sam? I guess everyone was involved. Too bad it was so short lived” Chuck laughed

“Oh no. We’re just getting started” Sam nearly spat the words


	10. Chapter 10

Sam’s POV

Chuck laughed. “Oh really what can you four do against me?”

“Us not much, but him”

Death stepped out. Revealing himself and Jack.

“He can do quite a bit.”

Chuck looked scared. “I’ll bring Dean back up. Just let me go.” He pleaded. Sam knew it was a bluff. He knew Chuck might temporarily bring him up, but cast him down again soon after.

Death laid his hands on Chuck. Suddenly Amara appeared looking confused. Then Death extracted what looked to be a golden mist from Chuck. He made a divide motion with his hands and the mist split into two revealing a darker more rusted looking mist. Death cast the darker looking mist down and laid the gold on Jack. Jack was enveloped in a golden mist before dissolving into him. He stumbled. 

Sam and Cas raced over to him to steady him.

“Are you alright?” Cas asked worriedly

“I think so” Jack responded

Sam had missed the kid so much. He went in for a hug. When they pulled away Death had disappeared. Probably back to Earth.

Sam looked at Jack “Can you do it? Can you bring Dean up?”

Jack closed his eyes and concentrated.

“I can’t” Jack tearily responded


	11. Chapter 11

Jack’s POV

Sam looked shell shocked.

“What do you mean you can’t bring Dean up?” Cas asked

Jack didn’t know if he could explain it. He wanted more than anything to save Dean, but he just couldn’t.

“I can reach his soul, but I can’t raise it. I don’t know why” 

Sam looked about ready to scream, but Cas took a calmer approach. 

“Maybe Chuck had a built in failsafe to ensure his damn ending stayed preserved”

Sam finished the thought “find the failsafe, and we can save Dean”

Jack eyed Chuck’s library. One book caught his attention ‘Brothers Throughout The Centuries’. He walked over and grabbed it. 

“This might give us somewhere to start” Jack said hopefully

He opened the book and started reading.

“It’s blank” Sam said

Jack sighed. Of course Chuck did this. “These were Chuck’s books so I guess I’m the only one who can read them”

If that was the case there was no need for the others to stand around.

“Cas why don’t you go to Hell and inform Rowena Dean can step off the rack now? I’ll keep looking for something to bring him up, but for now getting him off the rack is all we can do for him”

“Of course” Cas look relieved 

Sam spoke up “Can I-“

Jack interrupted “of course! Cas why don’t you take Sam with you?”

“Thank you”

Dean and Sam deserved to see each other. They’d been through a lot. 

Cas and Sam vanished. “Gabriel you’re an arc-angel. Can you read any of the books.”

“Not in this library no, but we have an arc-angel library I can dig through”

“There’s an arc-angel library?” Balthazar asked “where might that be?”

“There’s no way I’m telling you. Relics have a tendency to go missing around you”

“Guilty” Balthazar shrugged

Gabriel flew to the library. 

“So what should I do?” Balthazar asked

“Find the other angels. Me taking over for Chuck sent a shockwave through Heaven. Tell them what’s going on, and let them know if any of them need to speak to me I’ll arrange time for them to do so” 

Finally he was alone to read.

**Notes for the Chapter:**

> There will be a part 3. It won’t be as long as the first 2. Maybe 2-5 chapters


End file.
